Monoselective ortho-C-H functionalization of benzoic acids: A useful strategy for constructing aryl ring with specific substitution patterns

ORGN 620

Tiansheng Mei, mei7900@scripps.edu1, Ramesh Giri1, Nathan Maugel2, and Jin-quan Yu1. (1) Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, (2) Brandeis University
Pd-catalyzed iodination of ortho-C-H bonds in benzoic acids was developed. Importantly, monoselectivity was achieved by using bulky tetraalkyl ammonium salts as additives. The iodinated products are versatile intermediates for constructing various multi-substituted aryl rings due to the reactivity of the carboxyl group and iodide. The origin of this selectivity is under investigation.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008